An organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water

被引：31

作者：

Jaiswal, Pradeep Kumar ^{[1
]}

Biswas, Soumen ^{[1
]}

Singh, Shivendra ^{[1
]}

Samanta, Sampak ^{[1
]}

机构：

[1] Indian Inst Technol Indore, Indore 452017, Madhya Pradesh, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 48期

关键词：

MICHAEL-HENRY REACTION; ONE-POT SYNTHESIS; H BOND AMINATION; STEREOSELECTIVE-SYNTHESIS; CATALYZED SYNTHESIS; EASY ACCESS; DOMINO; CYCLIZATION; ARYLATION; ACTIVATION;

D O I：

10.1039/c3ob42034e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, mild, green, catalytic and general procedure for the direct synthesis of highly functionalized 1-methoxycarbonyl-2-aryl/alkyl-3-nitro-9H-carbazoles has been achieved in water medium via a one-pot domino Michael-Henry/aromatization reaction of methyl 2-(3-formyl-1H-indol-2-yl)acetates with aryl/ alky-substituted beta-nitroolefins under air using DABCO (30 mol%) as an organocatalyst. In addition, the bench scale synthesis can be performed without using toxic organic solvents and a biologically important new fused carbazole has been prepared.

引用

页码：8410 / 8418

页数：9

共 56 条

[1] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[2]

Ahluwalia V.K., 2009, GREEN SOLVENTS ORGAN

[3] Organocatalytic Domino Reactions [J].

Alba, Andrea-Nekane ;

Companyo, Xavier ;

Viciano, Monica ;

Rios, Ramon .

CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) :1432-1474

[4]

[Anonymous], 2008, CHEM BIOL CARBAZOLE, DOI DOI 10.1021/jo801132w

[5] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature [J].

Antonchick, Andrey P. ;

Samanta, Rajarshi ;

Kulikov, Katharina ;

Lategahn, Jonas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8605-8608

[6] Self-assembled monolayer coated gold-nanoparticle catalyzed aerobic oxidation of α-hydroxy ketones in water: an efficient one-pot synthesis of quinoxaline derivatives [J].

Bhattacharya, Tamalika ;

Sarma, Tridib K. ;

Samanta, Sampak .

CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (11) :2216-2220

[7] L-Proline catalyzed stereoselective synthesis of (E)-methyl-α-indol-2-yl-β-aryl/alkyl acrylates: easy access to substituted carbazoles, γ-carbolines and prenostodione [J].

Biswas, Soumen ;

Jaiswal, Pradeep Kumar ;

Singh, Shivendra ;

Mobin, Shaikh M. ;

Samanta, Sampak .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (41) :7084-7087

[8] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water" [J].

Butler, Richard N. ;

Coyne, Anthony G. .

CHEMICAL REVIEWS, 2010, 110 (10) :6302-6337

[9] Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[a]carbazoles [J].

Chen, Chin-Chau ;

Yang, Shyh-Chyun ;

Wu, Ming-Jung .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24) :10269-10274

[10] Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].

Cho, Seung Hwan ;

Yoon, Jungho ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005

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